Bruce Reynolds, the mastermind of the 1963 Great Train Robbery, has died aged 81, just months before the 50th anniversary of Britain's most spectacular heist. Reynolds, who had been in poor health for some months, was also the author of one of the most honest and literate of criminal memoirs, The Autobiography of a Thief.

The death was announced by Reynolds's son, Nick, a musician with the band, Alabama 3, with whom his father had occasionally performed.

Reynolds himself had been philosophical about his illness. Asked how he was feeling earlier this month, he replied: "Well, the axeman cometh."

"It really is the end of an era," said Leonard "Nipper" Read, the Scotland Yard detective who successfully pursued the robbers. "It was certainly a well-organised operation and Reynolds was the pioneer. It is a little piece of history."

In August 1963, a group of professional criminals from London carried out the elaborate robbery of the Glasgow to Euston mail train in Buckinghamshire, making off with £2.6m (worth around £33m in today's money). Most, but not all, of the robbers were later caught and sentenced to what were then record sentences of 30 years.

Reynolds initially fled the country and hid out under an assumed name in Mexico and Canada with his wife and young son. But he was caught upon his return to Britain in 1968. Tommy Butler, the detective who arrested him in Torquay, greeted him with the words: "Hello, Bruce, it's been a long time." To which Reynolds replied: "C'est la vie."

1968 Guardian report on Reynolds' arrest.
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Reynolds was jailed for 25 years, a sentence that even the late Metropolitan police commissioner, Sir Robert Mark, thought was excessive. In fact, one of the reasons the robbery became so well known was the length of sentences doled out by Mr Justice Edmund Davies, who said it was "a crime which in its impudence and enormity is the first of its kind in this country. I propose to do all in my power to ensure that it is the last of its kind … Let us clear out of the way any romantic notions of daredevilry".

In 1995, Reynolds wrote his memoirs which recounted, without sentimentality or self-pity, how he had embarked on a life of crime after initially seeking a job as a journalist but ended up working in the accounts department of the Daily Mail. He chose the title as a homage to one of his favourite writers, Jean Genet, author of The Thief's Journal.

Various television documentaries are now being lined up for the anniversary, with Reynolds approached by many seeking to capitalise on the event. Many of the robbers have already died: Charlie Wilson was shot dead in the Spain in 1990; Buster Edwards killed himself in 1994; Roy James died in 1997; Jimmy Hussey died last year after supposedly making a deathbed confession that he was the gang member who coshed the train driver, Jack Mills, who died of leukaemia seven years later. Ronnie Biggs remains in very poor health following a series of strokes. On the final page of his updated memoir, Crossing the Line, Reynolds remarks of Biggs: "When I see his frail frame, I see my own mortality. C'est la vie!"

There have been countless books on the robbery, of which Reynolds's remains the most lucid. It was also the subject of three films including Buster, in which Phil Collins played the eponymous role, with the part of Reynolds played by Larry Lamb. Various approaches had been made to Reynolds about making a film based on his autobiography.

The jazz-loving Reynolds, who lived out his last years modestly in Croydon, south London, wrote an article for the Guardian in 2008 about the £53m Securitas robbery of two years earlier, in which he quoted from David Mamet, William Burroughs and Chet Baker. He referred to the lines of Mamet's screenplay for the film, Heist: "Anybody can get the goods, the hard part's getting away." And he referred to Nipper Read's reflection that, perhaps, the Great Train Robbers would have carried out the robbery even if they had known that they were going to get caught.

Reynolds remained an avid reader throughout his life with JG Ballard, Norman Mailer and Scott Fitzgerald among his favourite authors. He also found himself on the road with Alabama 3, the band that produced the Sopranos theme tune, Woke Up This Morning.

He performed with the band on the song Have You Seen Bruce Richard Reynolds?

In his memoirs, Reynolds recalls how, just before the Great Train Robbery took place, he had smoked a Montecristo No 2 cigar: "The thought ran through my mind: I have brought Cuba to Buckinghamshire."

Now the anniversary will take place without the man who once said he had planned the robbery as his "line in the sand".